Chappaqua Vacation Rentals

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Browse Select Chappaqua Vacation Homes

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (86)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.

Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.

Charming Highland Falls Home < 2 Mi to West Point!

10.0 out of 10, Exceptional, (9)
"Wonderful front porch "
Charming Highland Falls Home < 2 Mi to West Point!

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

10.0 out of 10, Exceptional, (36)
"Perfect for our family’s visit to West Point. Great location "
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

2.0 star property
10.0 out of 10, Exceptional, (5)
"We had a very nice family weekend. There was plenty of room, the furniture and beds were comfortable, and the kitchen had everything we needed. Great communication with the owner"
The price is CA $454
CA $928 total
includes taxes & fees
Aug 11 - Aug 12
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

Quaint duplex with private yard. Walk to beach, dining, & shopping!

10.0 out of 10, Exceptional, (44)
"Needed a place to stay with our dog while visiting our granddaughters in a nearby town."
Quaint duplex with private yard. Walk to beach, dining, & shopping!

Spacious 4-bedroom house in charming Rye with AC

The price is CA $275
CA $625 total
includes taxes & fees
Aug 11 - Aug 12
Spacious 4-bedroom house in charming Rye with AC

Luxury 5BR 2BA Spacious Home NYC Free Parking + Office

Luxury 5BR 2BA Spacious Home NYC Free Parking + Office

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (36)
"Short trip. great place to stay . Very cozy . Family loved it "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Luxury NY Home 3BR with Easy Parking

3.0 star property
3.0 out of 10, (4)
"I was fooled by the pictures. Upon check-in, they require to zelle cleaing fee. When I finally got inside, I found absolutely nothing lux about this property, no comfort and hospitality. The broken floor welcome me, all 4 beds are broken, only 2 TVs, moldy restroom, zero confort. They left 4 towels for 6 people for 6 nights. I had to request more towels. I had to scoop water fromthe shower to flush in the toilet because water would not drain. Half roll toilet paper was left. If you take...
Luxury NY Home 3BR with Easy Parking

St Julian's Place - Large updated Apt @ 40 Min NYC

10.0 out of 10, Exceptional, (35)
"Loved everything about this place! Plenty of space for everyone, great location four minutes from the commuter train, having offstreet parking was a huge blessing! So much good I could say about this property, communication was wonderful, and having a laundromat just steps down the street was perfect for a laundry refresh in our trip! The neighborhood is quiet yet close to everything and well kept!"
St Julian's Place - Large updated Apt @ 40 Min NYC

Cozy 2 Bedroom, Near NYC, Easy Parking

10.0 out of 10, Exceptional, (1)
Cozy 2 Bedroom, Near NYC, Easy Parking

Modern 4BD/3BA w/Parking & deck & 29 min>NYC

9.8 out of 10, Exceptional, (17)
"The house was very clean and the check-in process was smooth. Host was very responsive. Overall we loved our stay and would definitely book again next time we're in the area!"
Modern 4BD/3BA w/Parking & deck & 29 min>NYC

Home: 2 Mi to Thayer Gate at U.S. Military Academy

10.0 out of 10, Exceptional, (2)
"Your home was amazing! My family and I enjoyed every minute! "
Home: 2 Mi to Thayer Gate at U.S. Military Academy

Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

2.0 star property
9.8 out of 10, Exceptional, (12)
"Clean and spacious apartment in a quiet neighborhood."
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (21)
"We had a great time and it was a very spacious and clean location "
The price is CA $861
CA $1,497 total
includes taxes & fees
Aug 12 - Aug 13
New Beach Home near Stamford Downtown/Shippan

Historic Hideaway with Lake Access!

9.8 out of 10, Exceptional, (17)
"The home was clean and the area is beautiful! It was a wonderful experience staying in a historic home and the owners were fantastic!"
Historic Hideaway with Lake Access!

Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town

10.0 out of 10, Exceptional, (3)
"The house was big enough for 2 families. It was very clean and comfortable. The property is beautiful and Cold Springs was the perfect spot for everything we wanted to do while in NY. The caretakers were very responsive and accommodating. We would definitely stay here again. "
Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town

New Jersey home, close to NY City Fun!

8.8 out of 10, Excellent, (6)
"My family and I stayed at Gloria's place for a few days to attend the funeral of our grandmother. The house was perfect for all of our needs and Gloria made us feel at home. "
New Jersey home, close to NY City Fun!

La Casita Bonita near NYC

5.0 out of 10, (2)
"Convenient location to upstate snd downtown NYC. All the rooms were good size. Appreciate the welcoming outside space both out front and in the back area. Plan to come back later this year."
La Casita Bonita near NYC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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